Tuscany Hilltowns Loop: Florence to Val d'Orcia

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The route · 7 stops

1
Florence
1 night
Base in Tuscany's Renaissance capital for the first night, picking up your rental car from Santa Maria Novella or the airport. A walk across the Ponte Vecchio and up to Piazzale Michelangelo at sunset sets the tone for the trip ahead.
Collect your rental car on Day 1. ZTL restricted zones cover the historic centre — do not drive into them, or face automatic fines passed on by the hire company.
2
Greve in Chianti
1 night23m · 27 km from previous
Gateway to the Chianti Classico wine country, 27 km south on the scenic SR222 Chiantigiana road. Stroll the triangular Piazza Matteotti with its porticos and enotecas, then book a cellar door tasting at a local estate in the afternoon.
Park on the edge of town and walk in. Most cantina visits need a booking — call a day ahead or ask your accommodation to arrange one.
3
Siena
2 nights32m · 38 km from previous
Tuscany's medieval rival to Florence, built on three hills with a UNESCO World Heritage city centre. The Piazza del Campo, the Duomo and the warren of contrade streets reward two full days of slow exploration. The food scene adds further reason to stay.
Drive to the city walls and park at Campo Reggio garage (closest to the Duomo). The historic centre is a ZTL zone — do not drive inside the walls.
4
Montalcino
1 night34m · 41 km from previous
A quiet hilltop town commanding views across the Val d'Orcia, famous for Brunello di Montalcino, one of Italy's most celebrated red wines. The nearby Sant'Antimo Abbey, a romanesque church in local travertine surrounded by olive groves, is worth the 10 km detour south.
Sant'Antimo Abbey holds Gregorian chant services most mornings — check the schedule online before making the detour south from Montalcino.
5
Pienza
1 night17m · 20 km from previous
Pope Pius II's ideal Renaissance city on a ridge above the Val d'Orcia. Walk the main corso, buy aged pecorino from a small shop on Via del Casello, and take the late-afternoon light from the edge of the town walls over the UNESCO landscape below.
The town is small. Park at the Parcheggio Pubblico just outside the walls and walk in. Fill up with fuel in Montalcino before driving to Pienza — stations are sparse.
6
San Gimignano
1 night1h 13m · 88 km from previous
Famous for its 14 surviving medieval towers, San Gimignano rewards an evening arrival when day-trippers have left. Try the Vernaccia di San Gimignano DOCG white wine before the short final drive back to Florence the next morning.
Arrive after 5 pm for a calmer atmosphere. Park in Parcheggio Montemaggio outside the south gate and walk up through the old town.
7
Florence
41m · 49 km from previous
Return the car in Florence and close the loop. Allow time for a farewell meal in the Oltrarno district before any onward train or flight.
Drop the car at the same pickup point unless you arranged a one-way. Same-day trains to Rome or Milan depart from Santa Maria Novella every hour.

Tuscany Hilltowns Loop: Florence to Val d'Orcia

The route · 7 stops

Florence

Greve in Chianti

Siena

Montalcino

Pienza

San Gimignano

Florence

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